Best Vacation Homes in Windsor
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $229/Night
For 7 Nights US $1,605
1948.27 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $507/Night
For 7 Nights US $3,547
1 Bedroom
1 Bathroom
Family Friendly
Resort
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $168/Night
For 7 Nights US $1,173
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $185/Night
For 7 Nights US $1,294
3465.98 ft²
9 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Parking
US $912/Night
For 7 Nights US $6,386
700 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
US $192/Night
For 7 Nights US $1,346
520 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $333/Night
For 7 Nights US $2,328
520 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $343/Night
For 7 Nights US $2,399
Windsor Luxury Rentals
39 Guests
16 Bedrooms
19 Bathrooms
Group Friendly
House
- Internet
- Child Friendly
- Security/Safety
US $3,967/Night
For 7 Nights US $27,770
3464 ft²
9 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $812/Night
For 7 Nights US $5,682
8 Guests
5 Bedrooms
4 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $604/Night
For 7 Nights US $4,226
1532 ft²
7 Guests
4 Bedrooms
2 Bathrooms
Cabin
- Fireplace/Heating
- Air Conditioner
- Internet
US $516/Night
For 7 Nights US $3,614
3000 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $487/Night
For 7 Nights US $3,410
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $477/Night
For 7 Nights US $3,338
3000 ft²
14 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $444/Night
For 7 Nights US $3,107
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $426/Night
For 7 Nights US $2,981
Windsor Pet Friendly Vacation Rentals
520 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $338/Night
For 7 Nights US $2,363
520 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $344/Night
For 7 Nights US $2,407
520 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $343/Night
For 7 Nights US $2,399
1950 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $420/Night
For 7 Nights US $2,937
8 Guests
4 Bedrooms
2 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Internet
US $402/Night
For 7 Nights US $2,815
1500 ft²
9 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $280/Night
For 7 Nights US $1,960
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $297/Night
For 7 Nights US $2,078
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $379/Night
For 7 Nights US $2,650
Windsor Large Vacation Homes
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Kitchen
US $234/Night
For 7 Nights US $1,637
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Kitchen
US $199/Night
For 7 Nights US $1,396
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Kitchen
US $252/Night
For 7 Nights US $1,763
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Kitchen
US $286/Night
For 7 Nights US $2,000
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $294/Night
For 7 Nights US $2,058
14500 ft²
32 Guests
15 Bedrooms
15 Bathrooms
Family Friendly
House
- Spa
- Fireplace/Heating
- Lake View
US $4,100/Night
For 7 Nights US $28,700
7 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Air Conditioner
- Internet
- Child Friendly
US $525/Night
For 7 Nights US $3,675
2000 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $383/Night
For 7 Nights US $2,681
Why Choose Rent By Owner for your Windsor Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Windsor
When should you plan your Vacation Rentals stay?
Timing your visit to this charming area can enhance your experience, as the region offers unique attractions and natural beauty throughout different seasons, making it essential to choose the right time for a memorable stay.
Peak Season Highlights
Summer (June to August)
Experience the warmest weather and vibrant outdoor activities in the region during these months, making it an ideal time for exploring the area's scenic beauty and local events.
Average Temperature Daytime: 75°F - 85°F - Nighttime: 55°F - 65°F
Fall (September to November)
Enjoy the stunning fall foliage that transforms the landscape into a tapestry of colors, attracting visitors seeking picturesque views and seasonal festivities.
Average Temperature Daytime: 60°F - 70°F - Nighttime: 40°F - 50°F
Off-Season Highlights
Winter (December to February)
During this period, the area offers a peaceful retreat with crisp air and snow-covered scenery, perfect for cozying up indoors or enjoying winter sports nearby.
Average Temperature Daytime: 25°F - 35°F - Nighttime: 10°F - 20°F
Early Spring (March to April)
As winter transitions to spring, you can experience fewer crowds while witnessing the first signs of nature's renewal in this picturesque destination.
Average Temperature Daytime: 45°F - 55°F - Nighttime: 30°F - 40°F
Weekly Weather Forecast for Windsor
How to Book Your Windsor Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windsor
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor patio or deck to relax and dine amidst scenic views.
- Take advantage of well-maintained gardens or landscaped yards for outdoor leisure.
- Make use of a barbecue grill to host cookouts in the fresh air.
- Discover nearby hiking trails or nature paths accessible from your rental.
- Utilize outdoor seating areas perfect for morning coffee or evening gatherings.
- Access to spacious lawns ideal for outdoor games and activities.
- Benefit from outdoor fire pits for cozy evenings under the stars.
Top Attractions Around Windsor
What attractions are nearby?
Enjoy a variety of outdoor activities and local attractions just moments from your vacation rentals, offering you the perfect opportunity to explore the scenic beauty and charming culture of this destination.
Family Activities
- Windsor County Fairgrounds: Experience family-friendly events and outdoor activities that offer a glimpse into local traditions and community spirit in the region.
- Vermont Institute of Natural Science (VINS): Discover wildlife exhibits and nature trails perfect for engaging children and teaching them about the area's rich natural environment.
- Downtown Windsor Historic District: Stroll through this charming district to enjoy boutique shops, historic architecture, and casual dining options suitable for all ages.
- Local Parks and Recreation Areas: Relax and play at scenic parks with picnic areas, playgrounds, and walking paths nestled within the region’s lush landscapes.
Adult Activities
- Windsor County Scenic Drive: Embark on a picturesque journey through the area's stunning landscapes, perfect for a relaxing day of sightseeing and appreciating Vermont's natural beauty.
- The Vermont History Museum: Delve into the region's rich history and cultural heritage, offering an engaging experience that connects you with the local story.
- Vermont Pub & Brewery Tour: Enjoy exploring some of the region’s renowned craft breweries, tasting locally brewed beers in a vibrant and welcoming atmosphere.
- Golfing at the Windsor Golf Course: Take advantage of the region's well-maintained golf courses, ideal for a leisurely round amid scenic surroundings.
Other Places to Stay in Windsor, VT
Path of Life Garden
Harpoon Brewery
Mt Ascutney Hospital and Health Center: Primary Care - Windsor
The Sustainable Farmer
Paradise Park
Brownsville Trail
South Congregational Church
American Precision Museum
Old Constitution House
Ascutney
Mount Ascutney
Mt Ascutney State Park
Windsor Travel Tips
How Can You Make the Most of Your Stay?
- Explore local attractions nearby: Take advantage of the region’s scenic beauty by visiting outdoor spots that showcase the area's natural charm, making your stay truly memorable.
- Plan your dining experiences: Savor the best of local cuisine at nearby eateries to enjoy authentic flavors and support the area's vibrant culinary scene.
- Check out seasonal events: Align your visit with local festivals or markets to immerse yourself in the regional culture and make lasting connections.
- Customize your accommodations: Choose vacation rentals that provide personalized amenities to enhance your comfort and ensure a relaxing stay in this destination.
Transportation Options
- Windsor Transit Services: Local bus options provide affordable and convenient transportation throughout the area, making it easy for you to explore without the need for a car.
- Amtrak Vermont Rail: The nearby rail station connects this destination to major cities, offering a scenic and comfortable way to arrive or depart from your vacation rental here.
- Rental Car Services: Several car rental agencies operate in the region, giving you the flexibility to discover Windsor and its surrounding attractions at your own pace.
- Taxis and Ride-Sharing: Taxis and ride-sharing services are readily available, providing quick and reliable transportation options during your stay in this destination.
Local Customs Options
- Local Craftsmanship: You will notice a deep appreciation for traditional Vermont craftsmanship reflected in the area's handcrafted goods and artisanal products.
- Farmers’ Market Traditions: Visiting local farmers' markets offers insight into the region’s agricultural customs and fresh produce that are cherished here.
- Seasonal Festivals: Participating in seasonal festivals allows you to experience the vibrant community spirit and time-honored celebrations of this destination.
- Respect for Nature: The community here emphasizes environmental preservation and outdoor etiquette, integral to enjoying the scenic landscapes in the area.
Frequently Asked Questions About Windsor?
1. What are the top vacation rentals in Windsor?
There are a lot of options in Windsor. If you plan on staying in the Windsor area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windsor:
- Meadow View- 35 Acres outside your door
- Sunset Cabin - your private romantic hideaway
- Long Range Mountain Views in West Windsor
- Inviting Vermont Home On Mount Ascutney!
- Snapdragon Inn
- Antique farmhouse with spectacular mountain view in a bucolic setting.
- Enjoy snowball fights or romantic nights in a 1BD vacation apartment
- Scandi-Chic Luxury Loft Near Okemo With Solo Stove And EV Charger
- Inviting Vermont Home On Mount Ascutney!
- Villa Near Biking and Hiking Trails
2. Which vacation homes in Windsor are best for families?
If you are looking for a family-friendly vacation home in Windsor, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windsor:
3. How many Rentbyowner vacation rentals are available in Windsor?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 72 in the Windsor area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windsor.
4. What is the cancellation policy for vacation rentals in Windsor, Vermont?
Cancellation policies vary depending on the property listing. You should review the specific rental’s terms before booking or contact the owner for detailed information about cancellations and potential refunds.
5. How can I ensure my reservation in Windsor, Vermont, is secure?
Reservations are typically secured through the booking platform with secure payment options. It’s advisable to read the host’s safety guidelines and verify their contact information to ensure a smooth experience.
6. Are there any additional fees associated with booking here?
Additional fees such as cleaning, service charges, or taxes are usually specified in the listing details. Always check the full breakdown of costs before finalizing your booking to avoid surprises.
7. What amenities are included in Windsor, Vermont, vacation rentals?
Amenities vary by property but commonly include essentials like Wi-Fi, kitchen facilities, and parking. Review the property description carefully or contact the owner directly to confirm the amenities available during your stay.
8. Is there a minimum stay requirement for booking a vacation rental here?
Minimum stay requirements can differ among listings. Be sure to read the booking details or reach out to the property owner to understand any restrictions or special conditions for your desired dates.
Windsor Top Rated Vacation Rentals
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $210/Night
For 7 Nights US $1,471
991.82 ft²
47 Guests
23 Bedrooms
7 Bathrooms
Family Friendly
Resort
- Private Pool
- Fireplace/Heating
- Pool
US $140/Night
For 7 Nights US $980
969 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
US $264/Night
For 7 Nights US $1,847
699.65 ft²
4 Guests
1 Bedroom
1 Bathroom
House
- Private Pool
- Hot Tub
- Spa
US $215/Night
For 7 Nights US $1,505
2000 ft²
7 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Spa
- Fireplace/Heating
- Pool
US $579/Night
For 7 Nights US $4,053
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $528/Night
For 7 Nights US $3,696
969 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
US $470/Night
For 7 Nights US $3,287
699 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
US $389/Night
For 7 Nights US $2,720
